(1S,2R,8R)-2,2-Dichloro-3,7,7,10-tetra­methyltricyclo­[6.4.0.01,3]dodec-10-en-9-one

Benharref, A.; El Ammari, L.; Berraho, M.

doi:10.1107/S1600536810040213

Volume 66
Part 11
Page o2911
November 2010

Received 1 October 2010
Accepted 7 October 2010
Online 23 October 2010

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.004 Å
R = 0.039
wR = 0.094
Data-to-parameter ratio = 16.6
Details

(1S,2R,8R)-2,2-Dichloro-3,7,7,10-tetramethyltricyclo[6.4.0.0^1,3]dodec-10-en-9-one

Ahmed Benharref,^a ^* Lahcen El Ammari ^b and Moha Berraho ^a

^aLaboratoire de Chimie Biomoléculaires, Substances Naturelles et Réactivité, URAC16,Faculté des Sciences Semlalia, BP 2390 Bd My Abdellah, 40000 Marrakech, Morocco, and ^bLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Avenue Ibn Battouta BP 1014 Rabat, Morocco
Correspondence e-mail: abenharref@yahoo.fr

The title compound, C₁₆H₂₂Cl₂O, was synthesized from [beta] -himachalene, which was isolated from essential oil of the Atlas cedar (cedrus atlantica). The asymmetric unit contains two independent molecules, in each of which the six-membered ring shows a half-chair conformation, whereas the seven-membered ring displays a boat conformation. The dihedral angle between the two rings is slightly different in the two molecules [63.22 (13) and 61.81 (14)°].

Related literature

For the isolation of [beta] -himachalene, see: Joseph & Dev (1968); Plattier & Teiseire (1974). For the reactivity of this sesquiterpene, see: Lassaba et al. (1998); Chekroun et al. (2000); El Jamili et al. (2002); Sbai et al. (2002); Dakir et al. (2004). For its biological activity, see: Daoubi et al. (2004).

Experimental

Crystal data

C₁₆H₂₂Cl₂O
M_r = 301.24
Monoclinic, P 2₁
a = 6.6680 (7) Å
b = 18.7760 (16) Å
c = 12.7696 (12) Å
= 90.430 (3)°
V = 1598.7 (3) Å³
Z = 4
Mo K radiation
= 0.40 mm^-1
T = 298 K
0.27 × 0.18 × 0.12 mm

Data collection

Bruker X8 APEXII CCD area-detector diffractometer
11524 measured reflections
5817 independent reflections
4348 reflections with I > 2(I)
R_int = 0.031

Refinement

R[F² > 2(F²)] = 0.039
wR(F²) = 0.094
S = 1.00
5817 reflections
351 parameters
1 restraint
H-atom parameters constrained
_max = 0.17 e Å^-3
_min = -0.17 e Å^-3
Absolute structure: Flack & Bernardinelli (2000), 1791 Friedel pairs
Flack parameter: 0.01 (5)

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IM2235 ).

Acknowledgements

We thank the National Center of Scientific and Technological Research (CNRST) for its support of our research.

References

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